ChemicalBook CAS DataBase List 3-BUTOXYANILINE

3-BUTOXYANILINE synthesis

8synthesis methods

Product Name:3-BUTOXYANILINE
CAS Number:23079-68-7
Molecular formula:C10H15NO
Molecular Weight:165.23

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23079-68-7
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Yield:23079-68-7 94%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol;water; for 1 h;

Steps:

3-butoxyaniline (S7)

A solution of S6 (692 mg, 3.54 mmol) in MeOH (5 mL) was flushed with nitrogen for 5 min. To a 50 mL round bottom flask under nitrogen was suspended 10% Pd/C (197 mg, 3.54 mmol) in MeOH/H2O (4:1) and the resultant suspension was added to the solution of S6. A balloon was filled with H2 gas and inserted into the flask and the reaction was purged with H2 gas for 2 min.The reaction was left to stir under a full balloon of H2 for 1 h, after which an aliquot was taken from the reaction, filtered through celite and cotton, and concentrated under reduced pressure.The aliquot was used for TLC monitoring which showed reaction completion. The reaction was filtered through a funnel packed with Celite. The filter cake was washed with MeOH and the filtrate was concentrated under reduced pressure, to give S7 (553 mg) as a dark yellow oil in 94% yield.

References:

Gandhi, Disha M.;Rosas, Ricardo;Greve, Eric;Kentala, Kaitlin;D.-R. Diby, N'Guessan;Snyder, Vladyslava A.;Stephans, Allison;Yeung, Teresa H.W.;Subramaniam, Saravanan;DiMilo, Elliot;Kurtenbach, Khia E.;Arnold, Leggy A.;Weiler, Hartmut;Dockendorff [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 17,p. 3788 - 3796] Location in patent:supporting information

109-65-9 Synthesis